Saturday, August 2, 2025

Jay Leno Was The Most Successful Late Night Host for Nearly 20 Years. Here's Why No One Respected Him Then and Now

 

"For what shall it profit a man if he gain the world,

but lose his own soul?

 

I seriously doubt that the majority of comedians are deeply religious – considering how much of their routines have been about blaming religion as the single greatest cause of what's wrong in society – but listening to them and indeed certain entertainers as well as progressives (frequently overlapping) you get the feeling that they overwhelmingly agree with this sentiment. It's usually referred to as "selling out" and in the terms of stand-up comedians it basically means its better to keep your edge and be respected by your peers – even if you only spend your life in nightclubs and the occasional TV special – then it is to always work in films and television but have to compromise your professional integrity to do so.

This is not uncommon in the entertainment industry: one sees it among independent filmmakers, rock musicians and even some people who work in television. But stand-up takes it to an extreme because its as close as any profession will come to agree with the idea of the starving artist mentality that so many critics hold too. In this argument it's better to die unknown accept among your peers – whether by natural causes or drug overdose – and never compromise then to have a long and successful career in Hollywood but give up your artistic integrity. This always struck me as a specious argument when critics gave it; comedians seem to be one of the few groups of professionals to take it seriously.

I've frequently reflected on this in regard to Jay Leno who for nearly twenty years was the number one name in late night with The Tonight Show but never seemed to enjoy the respect of his peers that his contemporary and eventual competitor David Letterman did. I wondered if this was just professional jealousy that he succeeded by compromising or whether this is genuine contempt for a man they consider a sell-out. Most of my life I would have said the former. Recent events have made me wonder.

Way back at the start of the 1990s Leno and Letterman were considered the chief rivals to get Johnny Carson's job hosting The Tonight Show when he eventually retired. Leno was the permanent guest host of Tonight; Letterman had the 12:30 AM spot.

Letterman was considered at the time the edgier comic during the 1980s and 1990s while many believed Leno had toned down the act he had used in his days as standup – and as a guest on Letterman – in order to make him more acceptable to the more traditional audience. Another critical factor came after GE purchased NBC and Letterman went out of his way to make jokes at the expense of his corporate parents, often satirizing General Electric's corporate structure and arguing that Warren Littlefield, then the head of programming, was a tool of the GE overlords rather than having a loyalty to entertainment.

In the minds of his fellow comics Letterman was simply doing was all entertainers and progressives are supposed to do: speak truth to power. This always leaves out two very important facts. First of all, many believe that the comedians first job is to make its audience laugh and everything else should be secondary. And when you do it on television, there is a very good chance the corporate overlords will be watching – and you'd better hope they have a sense of humor about being mocked on a nightly basis. (Believe me we'll come back to that.)

That's the other thing: Hollywood is a business first, everything else second. And if you're trying to contend for a job on the biggest stage in late night at the time, it might not be the best move to piss off the powerful because they will remember and they will make you pay for it. They can. That's the benefit of having power: something that entertainers and progressives tend to forget. You can speak all the truth you want to them, but they are under no obligation to listen or take you seriously. And as was said in Quiz Show: "The public has a short memory. But corporations they never forget."

And in Letterman's case, they didn't. How much of a role Letterman's barbs and gags played in him losing the Tonight Show will never be known for sure but it is worth remembering in an NBC retreat in the spring of 1993 when NBC program heads were trying to decide whether the flailing Leno should keep his job, Jack Welch stepped in and said that if it came down to a tie on everything else, he'd cast his vote for loyalty. And Letterman had definitely made it clear that while he was loyal to many things, it was not the network that was employing him.

His career, it's worth noting, could have come to an abrupt end when his contract ended in 1993. It was only because late night was now suddenly a competitive market after Carson retired that there was an opening. Letterman landed at CBS in the fall of 1993 and would be the number one in late night for the next year and a half. Then Leno took control of the ratings in the spring of 1995 and basically held them for the rest of his eighteen years (more or less) at the helm.

During Letterman and Leno's run there were many men who took a swing at late night. Chevy Chase was there and got in a flash, Magic Johnson didn't last much longer, nor did Keenan Ivory Wayans. Arsenio's moment ended not long after Leno took over. Eventually Jon Stewart would find a toehold but only when cable gave an opening in the late 1990s. Eventually Jimmy Kimmel would find a spot.

Most of the others who had success for those who had weekly shows on HBO: Dennis Miller, Chris Rock and eventually Bill Maher. Many of the others who tried in cable, such as George Lopez, would fail and Conan O'Brien eventually found a home there. But during this entire period Leno was the king of late night.

And this bothered the hell of so many other edgier comics, then and now. Leno never pushed the envelope with his material, never tried to be groundbreaking, seemed perfectly fine giving the audience what they want and never pushing the boundaries of his profession the way his contemporaries were. Leno took a fair amount of critical abuse and was frequently maligned by contemporaries including 30 Rock which openly attacked NBC about so many of its corporate decision. That it was only critically successful during a period when network television and NBC in particular were both struggling financially and that late night was one of the few places they were successful and never bothered them.

In this sense comedians knew that they couldn't do the one thing they wanted to: blame the audience. Entertainers know that edgy material is only going to give you a limited audience and that its easier to have mass acceptance if you play it safe. But it's never been something they could accept. So by and large they held their tongue through everything that happened and counted their blessings when Leno retired late in 2014.

Once he was gone late night could finally be played by the rules they wanted.

The rest is history…and as we've seen very soon, late night might be as well.

 

Last week after Stephen Colbert was fired Jay Leno was interviewed. This was a natural commentary. Leno was polite and said that it didn't make sense for comedians to be so political. He was polite and didn't name names but he did say whether from a commercial sense what logic it made to isolate half the country with your comedy.

As I've said before and will say again, late night was in serious trouble even before The Late Show was cancelled two weeks ago. Multiple articles had been run about how it was losing money across the board and Hacks had made it a central part of its current season. Fallon had needed to cut his programming to four nights a week, Seth Meyers had just had to cut his band for budgetary reasons and when Taylor Tomilson announced she was leaving After Midnight CBS wasn't willing to fund another host or spot. Everybody knew Late Night was in trouble. All Leno was doing was stating a very likely reason for it. This could be construed as speaking truth to power but surely it must have occurred to all of these smart people that having spent the last decade making fun of Trump had to have played at least a small role. And coming from a man who had spent nearly a quarter of a century in late night, it was hard to deny Leno might have some authority on the subject.

Yet to a man every single host in late night chose to attack Leno. And while he had been nice enough not to call anyone out, they all chose to call him out by name essentially trashing him and calling him a fool.

It is in these remarks more than anything else that these men – and they are all rich, white men; let's not for a moment call them  underprivileged – revealing their view of the world in a way that even their decade long attack on MAGA and Trump had done so. Confronted with a truth that disagreed with their personal worldview, they chose to double down on their original position and attack the messenger as being clueless and not knowing what he was talking about. They ignored the very real fact that many of them would likely not have the positions they did were it not for the work of one of their predecessors and chose to attack him on the fact that he had never been good at his job in the way that mattered. The fact that his audiences were generally always larger then his; that he had been in the business far longer than any of them, that he might know more about it than them, was meaningless.  

They chose to ignore the reality of the world they lived in and made the villains the corporations and the Republicans or just 'the man' who silenced Colbert because he was speaking his own 'truth to power'. That he and his colleagues were speaking that truth to smaller audiences than Leno ever did was irrelevant. He came from a different era. Never mind that he's lived through the same period they did, never mind that he's seen everything they have.

So many of these entertainers consider that their primary job is now to speak truth to power regardless of whether it changes anything or not. More and more comedians seem more inclined to consider themselves political activists first rather than entertainers. As I keep mentioning this has helped neither Hollywood as a business nor the progressive agenda. You would have thought November's election would have convinced both the Colberts of the world and their audiences of that reality. But it's clear that they remain in their bubbles.

Leno, I should add, was polite in his criticism. I'm sure somewhere in his soul it must be grieving him where late night. When he left late night in 2014, it was robust and healthy and even before Colbert was cancelled, it was becoming a ghost town with its demise getting closer every day. He didn't say that in his interview but it must have hurt on a personal level to see the timeslot where he had faced off with Letterman for twenty years – and which he usually won – will be empty again, this time for good. I'm not clear even now whether it bothers Colbert as much.

It's worth noting that all of the late night hosts have chosen to frame the cancellation of Colbert as a progressive rallying cry rather than concern for the health of their industry. Perhaps they chose to do so as an act of denial because the reality is the same regardless. I have little doubt that no matter what the fate of late night each host will no doubt console themselves with the same thing. "Sure we might have destroyed our medium, but at least we weren't like Leno and sold out." The difference is, of course, there almost certainly won't be a group of successors to Colbert and Kimmel and Fallon when this is over.

But why they should they care? They're all rich and active in Hollywood. They still have careers. Who cares if they had to torch their own industry to do it? That should make the left proud of them if nothing else. They did what the left wants them to: they will have burnt it all down. That nothing will ever grow from it again is irrelevant and only those who were there to observe will be behind to mourn. I will but what does it matter? It certainly won't to the future and that's all progressives care about.

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